Book Holiday Homes in Shady Side
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Featured Holiday Homes in Shady Side

Charming Historic Townhouse Steps From USNA

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

Quiet Relaxing Waterfront Suisse Chalet

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Shady Side Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Shady Side vacation homes are the perfect way for you to wing it.
Holiday houses in Shady Side let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Shady Side in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Shady Side adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Shady Side with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Shady Side vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Shady Side Holiday Homes essential information
Accommodation | 654 Holiday Homes |
---|---|
Lowest Price | NZ$526 |
Highest Price | NZ$804 |
Popular accommodation | Charming Historic Townhouse Steps From USNA, Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , The Cozy Crab- Your Charming Haven in Lovely North Beach!, Quiet Relaxing Waterfront Suisse Chalet, 421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!, Charming Downtown Annapolis. Stroll to all the Historic District has to offer. , The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill, ❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks |
More accommodations in Shady Side
Top trending hotels in Shady Side

Bay views with kayaks, bikes, fire pit, crabbing and more

Calloway Drive Retreat | House in Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Historic Inns of Annapolis
More ways to explore Shady Side
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^Subject to availability and chosen travel dates.